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<p>The inert carbon–carbon bonds of aromatic systems have long impeded the direct diversification of phenolic feedstocks into value-added scaffolds. Although enzymatic or energy-intensive strategies enable limited arene modifications, the controlled and programmable ring opening of phenols to unlock both skeletal and functional group diversity remains a fundamental challenge. Here we report an operationally simple and efficient nitrogenation strategy for cleaving phenolic arene rings, converting phenols into uniquely structured acyclic N-containing products including cyanopenta-dienoates, cyanopenta-dienamides and cyanopenta-dienoic acids. The method also enables scaffold hopping of corresponding arene rings, leading to important five-, six- and seven-membered N-heterocycles. The strategy demonstrates broad utility in late-stage modification of bioactive molecules, diversified skeletal remodelling of phenolic feedstocks, and the application of ring-opening products in polymer development. This approach transforms phenols into programmable linchpins for accessing underexplored chemical space, offering broad potential for synthetic chemistry and materials science.</p><p></p>

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Programmable arene ring opening unlocks the diversification of phenols

  • 期刊论文

  • 发表日期：

    2026年7月14日

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  • Yilei Huang,
  • Han Zhu,
  • Yichi Chen,
  • Teng Wang,
  • Zhibin Hu,
  • Ming-Hui Zhu,
  • Zengrui Cheng,
  • Hongwei Shi,
  • Junhong Meng,
  • Xi Wang,
  • Yixian Wu,
  • Ning Jiao

摘要

The inert carbon–carbon bonds of aromatic systems have long impeded the direct diversification of phenolic feedstocks into value-added scaffolds. Although enzymatic or energy-intensive strategies enable limited arene modifications, the controlled and programmable ring opening of phenols to unlock both skeletal and functional group diversity remains a fundamental challenge. Here we report an operationally simple and efficient nitrogenation strategy for cleaving phenolic arene rings, converting phenols into uniquely structured acyclic N-containing products including cyanopenta-dienoates, cyanopenta-dienamides and cyanopenta-dienoic acids. The method also enables scaffold hopping of corresponding arene rings, leading to important five-, six- and seven-membered N-heterocycles. The strategy demonstrates broad utility in late-stage modification of bioactive molecules, diversified skeletal remodelling of phenolic feedstocks, and the application of ring-opening products in polymer development. This approach transforms phenols into programmable linchpins for accessing underexplored chemical space, offering broad potential for synthetic chemistry and materials science.